The Bet
by sakurastardust
Summary: By chance, Drew and May meet and have a conversation in a cafe after his recent victory in a contest. Realizing he's in love with her, Drew makes a bet with her that can change the future status of their relationship. And it all started with a contest, a cafe, and a cup of coffee. One-Shot/ Contestshipping!


**I wanted to take a break from writing my drabbles on Steven Stone and May. I actually really ship Drew and May, but I find it harder to write about people who are portrayed as more arrogant than a typical "nice guy". Not sure why, maybe I'm just weird. Anyways please review and enjoy as always! **

Drew felt pretty smug as he walked out of the Goldenrod City Contest Hall, earning his fourth ribbon in the Johto region. He decided to spend time traveling on his own in Johto, hoping to become the Top Coordinator after being so close in the Hoenn and Kanto Grand Festivals. Looking back on those days, he felt like he improved and grew so much. He often looked back on the days when he was a selfish and inexperience trainer, even stooping low to the point where he had yelled at his Pokemon for not being good enough. He sighed, hoping that in the three years since then, he had improved and shown himself to be a better person toward his Pokemon.

Exhausted and worn out from the contest, Drew walked into a nearby café, ordering a cup of coffee. When his drink arrived, he stirred his spoon in his cup, absently staring out the window while tugging his green bangs, lost in his thoughts. He wondered about his other friends, a little shocked that he didn't see any of them compete with him, knowing that they were all traveling in Johto as well. He knew Solidad would have no trouble getting five ribbons in time for the festival, the woman had crushed him enough times for him to not to doubt her. Harley would probably pull through too, as flamboyant and odd as he may be. Then he thought about May, his rival and the girl who made his heart leap. She made him push himself harder, just so he could beat her in whatever they did. He wanted to strive so he could be considered worthy as her rival. He thought her about all the time, for the love of Arceus, he was so madly infatuated with her, he didn't even know if he could call her that anymore.

He kept staring out the window, one hand resting on his chin, until he heard someone slide into the booth across from him. He shifted his glance and met a familiar pair of bright blue eyes. He blinked a few times before his mind could comprehend that May, his rival and the girl he was in love with for the past three years, was sitting right in front of him, smiling. She looked the different than the last time he sae her. Her dark brown hair longer, and her face slowly losing baby fat, showing higher cheekbones. She still wore a bandana and wore her usual attire of shorts and a tank top.

"Hi Drew," she said, her tone as cheerful as always. "Congrats on your win today."

"Hello May. I didn't know you were watching," he said, genuinely happy she appeared.

"I just arrived, but I heard from people I was passing. I'm not really surprised you won anyways," she said with a smirk on her face. "I just saw you through the window and decided to surprise you."

"Of course it's not surprising I won. I hope you're ready to lose in the next contest," he said grinning.

She laughed and he missed hearing her loud retorts or protests. Instead, he was given twinkling laughs and giggles. He couldn't help but think about how she changed as she grew older. Of course they had changed, but she started off as an annoying little girl and then transformed into a gorgeous young lady. It just made him like her more. They talked more, time passing rapidly before them, the sky already dark. He made jokes, she laughed, they reminisced. It felt like forever since their last real conversation, since they were always arguing when they saw each other.

"So how many ribbons do you have now?" she asked, moving back to the topic of contests.

"After today, I have four. How about you?" He was actually very curious to know how many ribbons she had, his pride taking the best of him.

"I have four as well. Looks like we'll both probably see each other at the Grand Festival this year. I hope you've been training," confidence laced in every word she spoke.

"My, my," he retorted "Seems like somebody is confident. How about we make a bet."

"And what kind of bet would it be?" she inquired, raising an eyebrow.

"We're both skilled coordinators, right? So no hard feelings after, okay?"

"That's implied, Drew. Duh. Now, shoot," her tone impatient, showing her excitement.

"If I win or place higher than you in the Grand Festival, you need to become my girlfriend," he said, saying every word clearly, and he did his best not to stutter like an idiot.

She looked at him slowly, blinking as if to make sure she heard him correctly. He was about to say "just kidding" to cover it up until she shocked him with her response. He didn't want to feel ashamed if she declined. "Sure," she said, grinning widely.

"You're agreeing with my terms so willing. You're not going to back down later, are you?" he asked, feeling a tad bit skeptical.

"Who do you think you're talking to? First of all, I don't back down from challenges. Especially challenges made by you. Secondly, I'm agreeing because I know I'm not going to lose, so there's nothing to worry about," she said, sticking her tongue at him.

He gave her his famous smirk, that same cocky one he gave her when they first met three years ago. "Be prepared to be my girlfriend in two months. I promise that you won't regret making this bet later," he said, leaving money on the table and getting up. "It's pretty late, want me to walk you back to the Pokemon Center?"

"Sure. It'll be a rare opportunity since you'll still be single after I kick your butt in the contest." May got up and fixed her hair as she pulled her bag over her head.

As they both started to walk back to the Pokemon Center, he couldn't help but grin all the way there. He knew he looked stupid, but he could care less. She wouldn't even see it coming; he knew he had already won. In two months, he would have that trophy and her as well. Finally, she would be his.


End file.
